$115
Taxi from Highwood to Midway Airport
Schedule private airport car service from Highwood to Midway Airport. Flat-rate pricing, scheduled pickups, sedan, SUV and minivan options — same price both ways.
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Scheduled pickup — driver confirmed before your travel day
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Flat fare locked at booking — no surge, no meters
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Return pickup available from Midway directly to Highwood
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Flight tracking included for Midway arrivals
Vehicle Options — Highwood to Midway
Midway to Highwood Taxi Rates
| Vehicle | Passengers | Midway (MDW) | O'Hare (ORD) |
|---|---|---|---|
| Sedan | Up to 3 | $115 | $77 |
| SUV | Up to 4 | $120 | $82 |
| Minivan | Up to 6 | $130 | $92 |
Car seats are $15 each and must be requested when booking. Same-day and last-minute rides are welcome, subject to driver availability. Tipping is not enforced but is highly appreciated.
Arriving at Midway? Here’s Where to Meet Your Driver
Midway has one terminal. After baggage claim, go to the lower-level arrivals curb, Door 2. Your driver's name and vehicle are texted to you the day before your ride.
Midway at a Glance: One terminal · Concourses A, B, C · Southwest's Chicago hub · Usually shorter walks and faster baggage claim than O'Hare.
Explore Highwood
Highwood to Midway International Airport runs about 38 miles south via I-94 and the Stevenson Expressway — a North Shore to southwest side run for Southwest Airlines travelers from this compact Lake County city. Your driver confirms the flat fare and pickup before your travel day.
Highwood is a small city with an outsized restaurant scene — its dining district along Highwood Avenue draws people from Highland Park and beyond, and the concentration of good food in a walkable downtown has made the city a destination in its own right. The historic Fort Sheridan grounds to the north add architectural interest and Lake Michigan is close enough to shape the local character. The I-94 south and I-55 corridor connects Highwood toward Midway Airport.
Learn more about Highwood on the official municipal website.
Plan Your Highwood to Midway Trip
Leave time to spare. Aim to reach Midway about 2 hours before a domestic flight. The drive from Highwood is usually around 62 minutes, but rush-hour traffic, winter weather, and holiday travel can add time.
Check with your airline. Confirm your flight status, bag-drop deadline, and recommended arrival time before your pickup. Current screening information is available on the Midway TSA page .
Safety first. Your driver follows all traffic laws and cannot make up time lost because of a late start, so select a pickup time that includes a reasonable buffer.
Missed or canceled flight? Call dispatch immediately. Transportation back to Highwood is booked as a new trip and remains subject to driver availability. Full delay and missed-flight policy →
Book Your Ride from Highwood to Midway
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